Dad and I used to do it in 15 minutes...we had a system with our own responsibilities...On my own it takes about 30 min...I have no mast raising system....
I tie the jib sheet around the mast...run it through a hole in the forward end of the trailer and run it back onto the boat..I also hook the trailer winch to a second forestay...I then walk the mast up, pull the jib sheet tight and cleat it off..cleats are right near your foot so you kind've have to use your foot to hold the sheet down in the cleat as you pull it....this holds the mast up while I run around to the trailer winch and take in the slack....at that point I feel safe...
